The ex-war photographer used his charm to gain access to stars like James Dean and Frank Sinatra, then take shots that revealed the reality beneath the image

Phil Stern walks past a gallery of photographs that he took of James Dean. Photograph: Ric Francis/AP

If it hadn’t been for his razor-sharp reflexes, his stock-in-trade as one of the most talented and enduring photographers of Hollywood’s golden age, Phil Stern might have gone down in history as the man who killed James Dean.

In the spring of 1955, the two almost collided on a corner of Sunset Boulevard near the Chateau Marmont hotel. Stern was in his car, delivering negatives to Life magazine. Dean was on his motorbike, blithely crashing through a red light.

“I called him every four-letter expletive I could think of, and a few five-letter and six-letter ones too,” Stern recalled half a century later.

He didn’t care who he was talking to. Stern might have been known for his endearingly self-deprecating humour, but he was also a no-nonsense New Yorker who’d almost died in the second world war and he wasn’t about to kowtow to anyone, no matter how famous, young or beautiful. Dean, like so many other stars of his generation, clearly loved being treated like an ordinary human being, and took Stern out to breakfast at Schwab’s drugstore. And so a friendship – or, at least, an extraordinarily productive professional association – was born.

Stern, who died on Sunday at the age of 95, liked to call himself a “humble paparazzo”, but his real skill was to cut his subjects down to size as much as himself. In his images, his celebrity subjects weren’t untouchable icons but human beings caught in odd, goofy, telling moments: Dean poking his hair and his electric blue eyes out of a black polo-neck sweater, Frank Sinatra lighting a cigar for John F Kennedy at his inauguration ball, John Wayne in chequered hot pants in Acapulco.

These were shots the celebrities themselves cherished and loved. And as Stern got older, increasingly hampered by emphysema and the oxygen tank he had to carry with him, he’d get knocks on his door from Madonna or Michael Jackson asking for images from a bygone era. He lived in a modest townhouse next to Paramount Studios, and his visitors would walk in on lifesize cardboard cut-outs of Dean, Louis Armstrong, Sammy Davis Jr and Marlon Brando, who he referred to as his houseguests.

Telling moments ... Phil Klein’s backstage shot of Judy Garland. Photograph: Zuma Press, Inc/AlamyLike Hollywood at its best, Stern’s work was a felicitous mix of art and commerce. He knew his art history and had an unerring feeling for the humanity of his subjects, but he was also keenly aware of business opportunities when they arose and never hesitated to frame his shots differently if, say, it meant a chance at a double spread in a magazine instead of just a single-page feature. He vowed early in life not to suffer like his father, who’d been a Willy Loman-like travelling salesman, and was proud of using his back catalogue to put his four children through college and buy them houses.

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Hollywood was not his only subject. Some of his most haunting work is from his time fighting the Nazis in North Africa and Sicily: shots of his fellow soldiers marching past a graveyard, where many of them would soon lie, or praying by candlelight, or sitting huddled over a map.

When he returned from the war, he combined magazine work with regular stints as a stills photographer on the set of Hollywood movies. Unlike today’s paparazzi, Stern didn’t have to ambush his subjects or sneak up on them with long lenses. He won them over until they were glad to provide him all the access he wanted.

His charm and wicked humour were still fully intact when I met him in 2005. He had just, improbably, reassembled a collection of James Dean shots he’d long believed to be lost – shots of Dean, the midwesterner, eating apple pie with his friends in a modest Hollywood cafe – and used his hard-nosed negotiating skills to reclaim ownership of them.

He was a gracious host who didn’t stop cracking jokes, even when the tubes of his oxygen machine got tangled in the furniture and almost felled him. “You’re going to see a headline in tomorrow’s paper,” he said, “‘Renowned Photographer Dies Tripping On His Oxygen Tank’.”